Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-indol-2-one | HCID 58547665 | — |
| Reactant | (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate | HCID 86700141 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | HCID 86700272 | HCID 86700272 | — |
Reaction Steps
To a solution of (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (50 mg, 0.1 mmol) in dioxane (1.2 mL, degassed) was added 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (30 mg, 1.1 eq.), Pd(PPh3)4 (17 mg, 0.05 eq.), K2CO3(42 mg, 2 eq.) and water (0.1 mL). The reaction mixture was heated at 110° C. for 2 h, cooled and partitioned between ethyl acetate and brine. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give crude which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C31H32ClN2O4S: 563.2 (M+H+); Found: 563.3 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08987250B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-bd74937436c140ea8ac71baf65832397 |
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| Source note | uspto-grants-2015_03 |
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